


Experience

by ZombBean



Series: Night at the Hotel [1]
Category: At Dead Of Night (Video Game)
Genre: Cunnilingus, F/M, Foreplay, Hugos asleep for the most part, Jimmy is also a bit of a brat at times, Mostly you and Jimmy interacting, Vaginal Fingering, Vaginal Sex, but a gentle man none the less, hugos the asshole
Language: English
Status: Completed
Published: 2021-03-14
Updated: 2021-03-14
Packaged: 2021-03-21 19:29:11
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,650
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/30026733
Author URL: https://archiveofourown.org/users/ZombBean/pseuds/ZombBean
Summary: You came to the hotel in order to find subjects for the perfect painting. However, you find that you're enamored with more than just the local fauna.
Relationships: Jimmy Hall | Hugo Punch/Reader
Series: Night at the Hotel [1]
Series URL: https://archiveofourown.org/series/2208888
Comments: 7
Kudos: 48





	Experience

It was downpouring when you finally reached the hotel. A five mile walk in the frigid storm made your legs chafe and your nose runny, but you finally made it.

You’d been on your way to the remote island for a bit of inspiration. The trees, ocean and everything around made for the perfect scenery for you to capture on camera to use for future artworks. After all, personal references were always the best.

Stepping inside the Sea View hotel, you rung out the water from your shirt before stepping further in, the muffle of the storm echoing behind you as you made your way to the counter. Which, at first, was empty. Odd.

Dinging the little countertop bell, you waited for any sort of reaction before calling out, “Hello? Is anyone there?”

“Ah- yes, coming!” a rather rushed voice was heard before the clattering of a few items from a back room made you worry.

“Are you alright back there?” you exclaimed, tempted to move behind the counter to make sure the other being was alright.

“I’m fine!” you heard him holler back, though not without a wince and hiss of pain behind his words.

Stepping from the room behind the desk you were met with a rather curious looking man, about a head taller than you, with quite the odd haircut. He was dusting off his bowler hat, which he promptly placed back atop his head before meeting your gaze with a smile.

“Welcome to Sea View hotel! What brings you out here in this weather?” he chuckled, rubbing his left wrist.

You introduced yourself, telling him your name, and why you’d gone out to the middle of the ocean to a hotel in the middle of nowhere. It was for the arts of course. Something you greatly enjoyed. You also added that this was the time of year where the trees were in full bloom with beautiful flowers, as well as local fauna. 

He nodded as he listened, his expression changing from one of intent listening, to joy.

“You enjoy the arts as well?” he chimed, placing both hands on the counter and leaning, albeit, a bit too close over the counter. He was much like a cartoon in the way he moved, and while it was very odd, it was also… oddly charming?

“Yes, I’m quite taken with them!” you nodded, “I’m a painter you see, and I’m traveling to some beautiful local areas, and some not so local, so I can gather photos for a painting I’m working on,”

“A painting? I’d assume you didn’t bring it with you?” he chuckled, wrapping his hand up in a handkerchief.

“No, unfortunately the canvas was much too large to fit in any of my bags- besides the paint would smear, and I couldn’t chance it getting damaged, so for now? Photos will do nicely!” you looked to his hand, as you spoke, noticing the red stain forming on the cloth, “Are you sure you’re alright? Did you cut your hand badly?”

His smile faded to a sheepish look, waving off the matter, and tying the kerchief securely around his hand, “No no no, no worries- it’s a matter I can deal with on my own at a later time, as for you- uhh, you still need to check in… let’s see… you told me your name so we’ll just scrawl that down here… how many nights do you plan on staying?”

“If there’s room, I plan to stay a couple weeks, if I need to extend it more I’ll let you know ahead of time,” you tried to sound formal, but alas you were too much of a worry wart. But, since he’d pushed for you not to worry, you tried your best to ignore his injury.

“Two weeks, very well,” he paused scribbling down the information, as well as doing some calculations in his head- you assumed tallying up the amount it would cost for your stay, “Alrighty then, your breakfast and dinner is included in your stay as well, so no need to worry about that! Your total comes out to be… fourteen-hundred dollars…. Do you have the full amount?”

You had been saving your money back for this trip for a while- a couple years to be exact. So of course you had the full amount.

Pulling out your wallet, you took the bills from it and handed it over to the other his hand brushing against yours as you made the transaction. Whether intentional or not, it made you feel a wave of unease. Almost as if there was something he was hiding.

“Should all be there, let me know if it isn’t,” you rocked back and forth on your heels.

Flipping through the bills, he tucked it all away in the register. Soon after he flipped through a set of keys, pulling out a set and giving you yours for your stay- room 206.

As he reached out to hand you your key he held on a bit longer than needed, pausing before he let go, “So there’s a midnight show… would you care to see it? It’s a little performance I do for the guests where I play this crazy character who says things he really shouldn’t,” there was another pause, as if he’d been rejected before in the past.

“Umm…. sure, uhh… just let me get my bags to my room, get a nice hot shower and… well, dinner and a show sounds pretty damn good right about now,” you joked.

You swore he almost squealed in delight.

“Let me help you get your bags upstairs, part of the-” you cut him off before he could finish.

“Ahh… how about I take my things upstairs? I got a lot of heavy suitcases, and your hand really does look bad…. Tell you what, you take care of your hand and get ready for that show yeah?” you gave him a curt nod, making it hard for him to argue as you grabbed your bags and headed towards the lifts.

________________________

A hot shower and a nice change of warm clothes made the, now gentle, thunder in the background seem like a dream. Cuddled up in your nice warm pajamas, you were ready to settle down for the night- however… you did promise a certain someone that you’d be attending a show…. And judging by how empty the building was, you felt safe to assume that you’d be the only one attending.

At least there’d be dinner. That’s what made it a little more bearable. Not that you thought the show would be terrible or anything, but just the thought of being the only person in what was supposed to be an audience of people made you feel… well…. Awkward at best. 

“It’s gonna be ok, just… go to the show, and be a good guest right?” That's what you kept telling yourself.

Slipping on a pair of slippers, you made your way downstairs and to the main room. It was elegant, and very elaborate for such an old hotel. The walls were decorated with elaborate decor, a speaker system settled in the corners, and a grande stage for performances right in the middle of the back wall. 

“You look ready for bed,” the familiar voice of the man you’d met before was right behind you making you jump.

“Jesus… you scared the hell out of me… umm… shoot, I never did get your name,” well that was quite the awkward realization. 

“Jimmy Hall,” he smiled, giving a wink as a follow up to his cartoonish nature, “I figured I’d check up on you before show time!”

Something you didn’t have the heart to say made you feel awkward. Jimmy did seem like a nice guy sure, but the room… it was just so… empty.

“Can’t wait! I bet it’ll be a blast!” you smiled back, trying your best to lie, “What kind of entertainment did you say you did?”

“The easiest way to explain it is, dark humor,” he nodded, folding his hands in front of him.

“Oh! Okay cool, I’m kinda a fan of dark humor- how’s your hand doing by the by?” you looked to his hands.

“It’s just a cut, nothing bad,” Jimmy waved it off, obviously more excited about the show that was about to start.

When the show did begin, it was flashy to say the least. Lights managed to swirl around the room, and dramatic music firing up as you ate your meal. Honestly, you felt half starved after the rough day you’d had- and half of you was curious about what the show had in store.

It was… a bit crude for some people if you were honest. It didn’t bother you any, as most of your friends had made jokes to a similar caliber at some point. No dead baby jokes or anything, so at least his dark humor had a certain class to it. Some of the jokes were even… funny. You particularly liked the one about Mozart and the chickens.

Before you knew it an hour had passed, and the show was over. 

Clapping, you humored the rather funny fellow on stage. Perhaps he wasn’t as nerve wracking as you’d initially thought?

“So you really liked it?” he pulled a chair up to the table as you finished off your favorite drink.

“Yeah, you’re actually not that bad,” you chuckled, leaning forwards a bit in your seat.

You couldn’t help but notice he looked… lonely.

“I do try, though sometimes my humor doesn’t strike the right chords with people and they get all antsy and upset… dark humor isn’t for everyone!” he leaned back in his seat, separating what little space there was to begin with between the two of you.

“Does your family ever come by and watch your shows?” you asked.

He paused, and his hands shuffled awkwardly on the table a brief second, “I… no… I don’t- they passed on a while ago,”

Your smile faded, and you could feel the mental slap of awkwardness, “Oh… oh jeeze… I… I’m sorry I didn’t…”

“No, no, it’s quite alright. My mother… she’s been gone for some time now- since I was a teen, actually,” he scoffed, the subject obviously something he wasn’t used to speaking about.

“I didn’t mean to assume, or make things weird… uhh… y-your show really is great! I just… was wondering if there was company you shared your talents with besides your guests? You know, someone you’re close to?” you tried to recover from your mistake.

“No, just the guests- no one special in my life to share it with I’m afraid,” he looked away, as if embarrassed to face you.

“I see… well…” you crossed your legs in your chair, looking over the other, “Well, how old are you?”

“I… what? That’s… kind of rude to ask someone you’ve just met don’t you think?” he was defensive, and on one hand? It was kind of cute.

“No! No I mean… have you ever… you know, dated… anyone or something? I might have some friends of people I know…. You know what nevermind, this is kinda awkward isn’t it?”

There was a pause as a bolt of lightning struck somewhere off in the distance, and the low grumble that followed it echoed through the room.

“I just wanted an age range so I could-” you were cut off.

“Thirty five,” he spoke quietly.

“I… what?” you asked.

“I said I’m thirty five,” he repeated, a bit indignantly.

“Oh… you’re only thirty five?” you were honestly thinking he was a bit older for… reasons.

“How… old are you?” it was only fair of course. So you told him your age, “Oh… well, you look very nice for your age?”

The fact it came out as a question made you chuckle. Okay. Dude was cute not gonna lie. He wasn’t too old either, so bonus? Wait… bonus? Were you actually thinking he was your type now or something?

Oh how the standards have fallen.

“Did you hear me?” he repeated.

“I’m sorry, what?” you admittedly hadn’t been listening in your self doubt.

“I was asking if I looked… well… okay for err… my age?” he paused.

"Oh… well… you don't look all that bad honestly? Chocolate brown eyes, no grey hair, rather muscular build-" you nodded motioning to him. 

"But… the… erm… hair issue…? It's horrible isn't it?" he was well aware of what people might consider his flaws. 

"Well sure your missing hair," you chuckled, "But as long as you still have enough to grab and pull there shouldn't be any problem right?"

You froze when you realized how provocative that may have sounded, but the reference just flew over Jimmy's head. 

"Pulling my… why would I want you to pull my hair?" he grumbled. 

"It's… a sexual thing," you admitted, shrugging your shoulders. 

"How in the world…" he was baffled and intrigued but you could tell he wasn't asking. 

"I could show you but you might be uncomfortable if I do?" you smiled, teasing the thought of Jimmy feeling something so stimulating made you a bit excited. 

"S-show me?" he stammered, "Is it… really bad or…? Should I be worried?"

"Not at all, just a simple pull and an example of what someone would do afterwards," you assured him, motioning for him to come closer. 

Jimmy hesitated. He didn't know if he should trust you or not. After a few moments, he timidly scooted closer and leaned towards you, his curiosity too much for him. 

Chuckling to yourself you reached up and tangled your hands into that messy mop of hair- which, while he was balding, what remained was surprisingly thick and soft. Gripping it tightly in your fist you heard a grunt of disapproval before tugging his head backwards and placing your mouth on his neck, earning you a shiver and a groan from the other. 

Desperate hands clung to your front as a deep shade of pink ran up his neck, ears, and cheeks. Giving him a few more kisses just ended in him biting back another surprised moan before you let go. 

"Y… you little minx…" he stammered, rubbing his neck and scrunching his head to his shoulders to protect his obviously sensitive neck. 

"Like I said, it's a kink thing. A sex thing," you added, although the reddining cheeks of the other told you he lacked experience. 

"Ah. I… i see," he coughed a bit to clear his throat. 

Biting your bottom lip you debated a few thoughts in your head, "Have you ever even had sex Jimmy?"

The look of absolute horror on his face that you just plain asked him almost made you laugh. 

"I...I… I wh… what?!" he couldn't find the words. 

"Cause well… you're cute and I'd like to think maybe we could be good friends… want me to… well… show you what sex is like?" you couldn't help but reach out and hold his hand, "You can say no, no worries,"

Jimmy opened and closed his mouth. Thinking it over in his head, he closed his eyes and weakly, gave a nod. He was morbidly curious. 

"Okay, well first off do you have any experience? I need to know so I can walk you through it," you calmly rubbed his hand with your thumb. 

"S… self experimentation… you know what most young men go through? I've kissed a woman, held one, but since I started… losing my looks and to be honest my… temper sometimes, I've yet to... " he cleared his throat again. 

"Okay, well luckily I'm not a virgin, so walking you through everything will be easy," you reassured him. 

"O… okay, s… so when should we…?" he stammered. 

You smiled at him and squeezed his hand, "Meet me in my room in an hour,"  
______________

An hour wasn't too long to prepare but it was enough time for you to get everything you needed out of the way. Some lube in case he got too eager, a vibrator for stimulation, a cute nightgown, and a condom for safety. 

You expected him at any moment, but he was running a bit late. Just when you thought he wouldn't show, there was a knock at the door. 

"It's okay, come on in!" you hollared after, turning and sitting in your gown. 

Jimmy entered the room with all the timidness of a frightened rabbit. Wide eyes staring as he looked you over.

"O… oh dear, umm, you look… lovely," he half chuckled as he tried to break the ice. 

You motioned for him to come over and he settled down next to you. Placing a hand on his cheek, you felt a little bad as he leaned into it. Touch starved would accurately describe him at the moment. 

"Your hand is so warm," he cooed, placing a hand over top of yours. His hand was a slight bit chilly, his nerves probably gave him chills. 

"We can take this slow, sound good?" you spoke softly as you leaned in and gave him a peck on the lips. He froze. 

Shaky hands moved from yours to your shoulders, pulling you closer slowly until his lips were pressing a bit roughly into your own. His grip moved to the small of your back, and his mouth trailed kisses over lips and cheeks, going as low as a jawline before he pulled away in embarrassment. 

"S… sorry I… I'm not used to... " he held your hand and gave the top a kiss. 

"Such a gentleman! No worries sweetie, I'll take good care of you," you hummed, leaning in for more soft kisses. 

But kisses weren't what you two had set out to do tonight. Tonight you were going to ride the hotel owner, and give him the time of his sweet life. He was so sweet and adorable you couldn't miss the opportunity. 

"So umm… what should we do first?" he spoke quietly, his hand rubbing over yours with his thumb. 

"Lay back and let me take care of you," you grinned, pushing the other gently onto the bed. 

Jimmy looked up at the ceiling for a small moment before taking a deep breath and letting out slowly. Closing his eyes he moved his hands to cover his face. He was embarrassed, scared, and a bit excited. 

Moving your hands to his shirt, you carefully unbuttoned his shirt, trailing kisses from his collarbone down his chest, to his stomach. He twitched and shivered under each small touch, and it made your stomach flutter knowing how much you made the other squirm. 

"I'm going to do something nice for you okay? Just try to relax," you warned him as you unbuttoned his pants and began to take them off. 

"O-okay, Jimmy nodded, bringing a hand down from his face to look at you. 

Shuffling around his pants, you tucked down his underwear and, to your surprise, found he was pretty well endowed thickness wise. You couldn't really wrap your hand around it, but it was sensitive to your touch, twitching as you looked him over. Length wise he was a little more than average. 

"What are you staring at?" he sounded a bit distressed, as if he thought something was wrong. 

"Just looking at how girthy you are Jimmy… you're pretty impressive you know?" you placed a kiss to the head of his cock. 

"I a-ahhh! A… am?" he let his head roll back onto the pillow. God he was so sensitive and pent up! It was adorable! 

Taking his cock, you lowered your head down and took him in. Letting your tongue run along the slit of his cock, and down the pulsing vein on the underside. 

Jimmy let out a whimper at first but his fists balled up on the sheets of the bed, and his voice hitched with a gasp. Feeling you wrapped around his length, he let out a deep throaty moan. 

"Like that don't you?" you questioned, taking the whole length down your throat. Which was pretty difficult given how thick he was. 

Jimmy's hips hitched, and a free hand grasped the back of your head, tangling his fingers in your hair and pressing himself deeper down your throat. You gagged a bit but let him, feeling his shaking hands press you down and pump his cock down your throat. 

He'd pause periodically letting you come up for air, though it was mostly because he didn't want to cum too soon. You could tell by the look of determination on his face. 

When he couldn't take it anymore he grabbed your arm and pulled you up to him, his mouth capturing yours in a deep kiss. He tasted you, taking his time with tender delicate kisses. 

You could tell he was really trying. Like REALLY trying to impress you. His hands running over your breasts and sides. Gripping your hips he pulled you on top of him. He ran his piano fingers over your stomach, inner thighs, and up to your breasts again. He explored every inch he could reach. 

"Want more?" you asked, reaching down to touch his face. 

He relaxed into your touch, drunk on love, he nodded. He seemed more compliant and needy, and you could tell by his throbbing erection he really wanted you. 

"Okay but you gotta get me ready first ok? Get me stretched out and wet, well… stretched out anyway," you adjusted yourself and pulled down your panties, showing the other how wet you really were. 

Jimmy's eyes widened as he carefully reached over and ran his fingers over your mound, down to the lips. His fingers slid over you and he found himself coated in your slick fluids. He shivered, before furrowing his brows and bringing it up to his lips, dipping his fingers in and moaning. 

"Better than I could have dreamed... " he shuddered. 

Ok. So that was pretty fucking hot. The way he got so riled up over the flavor of you was more than enough to make you wanna jump his bones. But you had to be patient, maybe even cum once because WHOO BOY was he not a cock you just wanted to slap your pussy on and call it good. 

"Want to taste more?" you purred, bringing your hips closer to his chin.

His ecstatic nod was immediate. He tucked his arms under your legs, luckily smart enough to catch your meaning. 

Bringing your hips to his face, you were straddling his mouth, and a hot wet tongue slid over your opening. The noises he made were feral, like a man who hadn't eaten in weeks. He explored, dipping his tongue inside you and eventually flickering over your clit. 

"Oh…" you jumped. 

Jimmy noticed. He was smart. 

He ran his tongue over the sensitive bud again, enjoying making YOU jump for once. He let out a deep throaty laugh, lapping and playing with you. He seemed overjoyed.

“T-tables have turned haven’t they?” he hummed, continuing to please you.

“N-nope, just letting you enjoy everything… you are enjoying it right?” you purred, running your hands through his hair.

Jimmy, a bit indignant at being told he was ‘let’ to enjoy himself, blew a raspberry. He could be so childish. Though you couldn’t help but shiver and laugh. It felt really good, and his playful demeanor was more than welcomed.

“Feel how slick and wet I am? You already got me to cum once… how’s that make you feel?” you pulled away, earning a disappointed whimper.

“But you didn’t moan like… well…” he scoffed as if expecting something.

“Like in porn? Most of the time women don’t- it’s only after a couple orgasms when we’re really sensitive we make noise, some people are noisier, and some won’t make noise no matter what you do,” you explained, sitting next to the rather confused man.

“It’s… not a performance problem… is it?” he sounded disappointed in himself.

“No, it’s just starting is all! Now how about we try out that nice warm cock of yours?” you grinned, taking the others hand and smooching the knuckles.

Jimmy let out another breath, as if he’d been waiting the whole time for the main event. 

Positioning yourself over his length, you took the tip and slowly pressed him inside you. Inch by agonizing inch, you felt your insides pull at you in a comforting, pleasurable way. Jimmy gripped your hips, trying his best not to move. You said he was bigger than normal after all.

“Hmm… so nice… you fill me up so well Jimmy,” you purred into his ear, getting that last few inches of delicious cock deep inside you.

His happy, delighted moans were music to your ears as his hips jumped, trying to get more. Surely you were well adjusted now right? 

"More please…" he begged, gripping your hips tightly as he thrust upward. 

The sudden jolt made you gasp, taking him was no easy challenge. 

Placing your hands on his chest you eased back up, and down again, getting a steady rhythm of your hips moving. You could feel him rub against your clit as you rode on top of him, but it wouldn’t be enough and you knew this.

“Wanna make me feel even better Jimmy? Give you a bit more control?” The idea seemed to appeal to him because he was now staring at you through half lidded eyes, nodding, “Okay then take your hand, and rub your thumb against me here,”

You took his hand, leading it to your mound and helping him rub against that oh so sensitive area, rubbing in a forwards and back motion. It made it feel so much better. Gasping, you ground your hips forward, making Jimmy gasp and continue his administrations faster. 

“F-feels good,” he groaned, gripping your hip with his free hand and thrusting his hips upward desperately, he panted mumbling under his breath as he said your name, the words so delicious as they left his lips.

“F-fuck, I’m gonna… I’m gonna cum!” you gasped, grinding harder into his cock.

It didn’t take much for Jimmy to cum, feeling thick streams sputter inside you. It was enough to drive you over the edge, his thumb still swivelling around your clit as you came.

As you moved his hand away he was confused, but the replacement of your body against his made him feel better. Hesitantly, he wrapped his arms around you, resting his head atop yours as he pulled out and lazilly turned you to your side. Nuzzling into your hair he took a deep breath, content to have you with him.

“That was… wonderful,” he admitted, not really wanting to let go.

“Good it was supposed to be!” you laughed, resting your face against the crook of his arm, “Maybe we can find out what some of your kinks are later,”

You were mostly joking, but it had Jimmy in thought.

“Kinks…? More dirty talk, and teasing I presume?” he half huffed, that pout coming back.

“Who knows? Maybe you’ll like bondage, or gagging someone, or hell maybe you’ll like predator and prey play?” you mused, trying to give him an idea.

“What in god's name is predator and prey play?” his brows arched.

“It’s where one person gets chased around by another person and when they get caught the other fucks them mercilessly,” you noted, taking your hand and letting your fingers tangle in his.

Jimmy’s eyes went a little dark in that moment. It was almost as if he was possessed by another person altogether. Rubbing his chin, he looked down at you, rather liking the idea.

“We can try it sometime if you want? I don’t mind,” you hummed, a bit tired now that it’d gotten so late.

Jimmy held you close, like a protective brick of a man, “You don’t say? Well… I rather like the concept of that,”


End file.
